Gloucester Getaways: A Day Trip from Boston

August 26, 2024 / Food and Drink, History/Maritime, Things to Do & See

by Gabriella Amarel

Thinking of venturing out of Boston for a day but want to stay close? Look no further than Gloucester, a charming coastal town north of the city, swimming in maritime history, artistic flair, and delicious seafood.

Imagine a day trip where you can stroll through historic streets lined with colorful shops, savor fresh seafood at waterfront restaurants, and immerse yourself in the rich history of a coastal town that has captured the hearts of artists and sailors for centuries.

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A Train Ride to Remember:

The best part? You can ditch the car and make it a breeze with the MBTA Commuter Rail from North Station. Picture yourself relaxing in a comfortable train seat, watching the bustling city of Boston fade into the distance as you glide towards the tranquil shores of Gloucester. The journey itself is part of the adventure.

 

A Downtown Adventure:

Once you arrive in Gloucester, step off the train and into a world of quaint shops, art galleries, and historic buildings. Explore the charming downtown area, where cobblestone streets lead you to hidden gems around every corner.

Uncover unique finds at Design of Mine, a boutique known for its stylish clothing and accessories. Whether you’re looking for a trendy outfit or a special piece of jewelry, Design of Mine is sure to have something to suit your taste. Treat yourself to some of the finest olive oils at Cape Ann Olive Oil Co. and find the perfect pair of shoes at Mark Adrian Shoes. Discover a hidden gem among the stacks at Dogtown Books, a cozy bookstore brimming with new and used titles.

Learn about Gloucester’s rich past at the Cape Ann Museum, a must-visit to learn about Gloucester’s rich history. The museum’s exhibits showcase the town’s maritime heritage, artistic legacy, and cultural significance.

Stroll through the vibrant streets and be captivated by the artistic energy. Stop by a gallery or two, to admire local artwork. Gloucester has a thriving arts scene, and you’ll find a variety of galleries showcasing everything from paintings and sculptures to ceramics and jewelry.

New England style lobster roll at Decklyn's in Gloucester, MA

Decklyn’s

A Culinary Delight:

Gloucester’s vibrant culinary scene is a feast for the senses, offering a delicious array of dining options that showcase the region’s fresh ingredients and diverse influences. From classic New England fare to international flavors, there’s something to satisfy every palate. Here are a few must-visit restaurants that will leave you craving more:

George’s Restaurant and Bar:

Step back in time at George’s Restaurant and Bar, a classic New England eatery that has been a local favorite for generations. Enjoy a wide variety of dishes, including hearty breakfasts, delicious lunches, and satisfying dinners. Whether you’re craving a juicy burger, a comforting pasta dish, or fresh seafood, George’s has something to satisfy every palate.

Decklyn’s:

For a waterfront dining experience, head to Decklyn’s. This charming restaurant offers stunning harbor views and a lively atmosphere, perfect for a relaxed meal. Indulge in their fresh seafood dishes, salads, and sandwiches, all prepared with the finest ingredients.

Harbor Tours Gloucester MA

Adventure Awaits:

Feeling a bit more adventurous? Consider a harbor tour with one of the many local companies. These tours offer a unique perspective of the city and its surroundings. Explore the rugged coastline, spot marine life, and learn about Gloucester’s rich maritime history from experienced guides.

  • Cape Ann Harbor Tours: Offers a variety of tours, including lobster tours, lighthouse cruises, and river trips.
  • Beauport Cruiselines: Provides scenic harbor cruises with options for lunch, dinner, and dancing.
  • Cape Ann Cruises: Offers public and private yacht cruises, including sunset cruises and fishing charters.
The Cut exterior

Nightlife and Entertainment:

After a day of exploring, head to The Cut for a lively atmosphere, innovative cocktails, and live music. This popular spot is known for its creative drink menu and often hosts local bands and DJs.

A Perfect Ending:

As your day winds down, take a moment to soak in the beauty of the Gloucester Harbor. The setting sun paints the sky with vibrant colors, creating a picture-perfect ending to your day trip. Find a cozy spot on the waterfront, grab a drink, and watch the boats gently bob in the harbor.

Plan Your Escape:

Whether you’re a history buff, an art enthusiast, or simply seeking a relaxing escape from the city, Gloucester has something for everyone. So, pack your bags, hop on the MBTA Commuter Rail, and discover the charm of Gloucester, MA!